2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol (YMDB01373)

Identification
YMDB IDYMDB01373
Name2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol (alpha-Terpineol) is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent.Terpineol has a pleasant odor similar to lilac and is a common ingredient in perfumes, cosmetics, and flavors. α-terpineol is one of the two most abundant aroma constituents of lapsang souchong tea; the α-terpineol originates in the pine smoke used to dry the tea. [Wikipedia]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (+)-alpha-terpineol
  • (+)-p-menth-1-en-8-ol
  • (1R)-alpha,alpha,4-trimethyl-3-cyclohexene-1-methanol
  • (6R)-p-menth-1-en-8-ol
  • (r)-(+)-alpha-terpineol
  • (R)-2-(4-Methyl-3-cyclohexenyl)isopropanol
  • (R)-alpha,alpha,4-trimethylcyclohex-3-ene-1-methanol
  • (R)-p-Menth-1-en-8-ol
  • (S)-(-)-p-Menth-1-en-8-ol
  • 1-alpha-terpineol
  • 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol
  • 2-(4-methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol)
  • 2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol
  • 3-Cyclohexene-1-methanol, &alpha
  • 3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, (S)-
  • alpha-terpinenol
  • alpha-terpineol
  • alpha-terpineole
  • alpha-terpinol
  • alpha,alpha,4-Trimethyl-3-Cyclohexene-1-methanol
  • L-alpha-terpineol
  • Menth-1-en-8-ol
  • p-Menth-1-en-8-ol
  • Terpenol
  • Terpineol
  • Terpineol schlechthin
  • Terpineol, alpha
  • (R)-alpha-Terpineol
  • (1R)-a,a,4-Trimethyl-3-cyclohexene-1-methanol
  • (1R)-Α,α,4-trimethyl-3-cyclohexene-1-methanol
  • (R)-a,a,4-Trimethylcyclohex-3-ene-1-methanol
  • (R)-Α,α,4-trimethylcyclohex-3-ene-1-methanol
  • (R)-a-Terpineol
  • (R)-Α-terpineol
  • (+)-a-Terpineol
  • (+)-Α-terpineol
  • a-Terpineol
  • Α-terpineol
  • 2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol
  • Lily OF valley
  • DL-alpha-Terpineol
  • alpha-Terpineol, sodium salt
  • D-alpha-Terpineol
  • (S)-a-Terpineol
  • (S)-Α-terpineol
CAS number98-55-5
WeightAverage: 154.2493
Monoisotopic: 154.135765198
InChI KeyWUOACPNHFRMFPN-UHFFFAOYSA-N
InChIInChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
IUPAC Name2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol
Traditional IUPAC Name(+)-α-terpineol
Chemical FormulaC10H18O
SMILESCC1=CCC(CC1)C(C)(C)O
Chemical Taxonomy
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point37.5 °C
Experimental Properties
PropertyValueReference
Water Solubility0.71 mg/mL at 25 oC [LI,J & PERDUE,EM (1995)]PhysProp
LogP2.98 [LI,J & PERDUE,EM (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.56 g/LALOGPS
logP3.17ALOGPS
logP2.17ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)19.4ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.46 m³·mol⁻¹ChemAxon
Polarizability19.07 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
AniseFDB014552
CitrusFDB014552
FloralFDB014552
LilacFDB014552
MintFDB014552
OilFDB014552
PineFDB014552
TerpeneFDB014552
WoodyFDB014552
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-052f-9200000000-ae93728615d3c506a1ceJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-a6b151ba8e67f64241acJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01qi-9620000000-6c96b32bd4033639edd2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0540-5900000000-cda96dbf2d059d85a3c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-ef81a719227e0ca1dabcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-057l-9000000000-f219b3601875dbade6b9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1900000000-3e8ebaa4ae0750710d12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-9600000000-de13f72872a89c9b2a52JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0le9-9100000000-f6bc053d285b0f1e22f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-0b1926cd4fc400a61e84JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-3900000000-b512881ea0d1ea051199JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-9400000000-90c166242df69d6dee01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-118ad26f2b30eb1cab8bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda80JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9500000000-4ef1ecf90c5038ba6f9eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-5900000000-4a5f3c6978eb2913079eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mn-9100000000-e7d43b2d0a8d389277d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-c647649541c827cabb3bJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
  • Kogan, G. L., Filipp, D., Arman, I. P., Leibovich, B. A., Beliaeva, E. S. (1991). "[Cloning of segments of the Drosophila melanogaster genome using artificial chromosomes of the yeast Saccharomyces cerevisiae]." Genetika 27:1316-1323.1761208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID300
HMDB IDHMDB04043
Pubchem Compound ID17100
Kegg IDC09902
ChemSpider ID13850142
FOODB IDFDB014552
Wikipediaalpha-Terpineol
BioCyc IDCPD-4887